i EXTRACTION OF ESSENTIAL OILS FROM JASMINE FLOWER US …

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EXTRACTION OF ESSENTIAL OILS FROM JASMINE FLOWER US ING

SOLVENT EXTRACTION BASED ON PETAL CONDITION

MUHAMMAD SAIFUDDIN BIN IDRIS

A thesis submitted in fulfillment of the requirements for the award of the degree of Bachelor of Chemical Engineering

Faculty of Chemical & Natural Resources Engineering

Universiti Malaysia Pahang

MAY 2008

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I declare that this thesis entitled “Extraction of essential oils from Jasmine

flower using solvent extraction based on petal condition” is the result of my own

research except as cited in the references. The thesis has not been accepted for any

degree and is not concurrently submitted in candidature of any other degree.

Signature : .................................................... Name of Candidate : Muhammad Saifuddin bin Idris Date : 15 May 2008

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DEDICATION

Special dedication to the memory of my beloved mother and father, Miah bt Bidin

and Idris bin Sharif, my aunty and uncle and all my family members that always

inspire, love and stand besides me, my supervisors, my beloved friends, my fellow

colleagues, and all faculty members

For all your love, care, support, and believe in me.Thank you so much.

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ACKNOWLEDGEMENT

Praise be to God for His help and guidance that finally I’ll able to complete

this final year project as one of my requirement to complete my study.

First and foremost I would like to extend my deepest gratitude to all the

parties involved in this research. First of all, a special thank to my supervisor Mr.

Syaiful Nizam bin Hassan for willingness in overseeing the progress of my research

work from its initial phases till the completion of it. I do believe that all their advice

and comments are for the benefit of producing the best research work.

I am grateful to the staff of Faculty of Chemical Engineering of University

Malaysia Pahang for their cheerfulness and professionalism in handling their work.

In preparing this thesis, I was in contact with many people, researches, academicians

and practitioners. They have contributed towards my understanding and thoughts.

In particular, my sincere thankful is also extends to all my colleagues and

others who have provided assistance at various occasions. Their views and tips are

useful indeed. Unfortunately, it is not possible to list all of them in this limited space.

And last, but not least I thank my mother’s and other family members for their

continuous support while completing this thesis.

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ABSTRACT

Pure Jasmine essential oils are primarily used in the perfumery industry and have

a very high commercial value due to its therapeutic properties. As Jasmine essential oils

are composed of heat-sensitive chemical compounds, the use of conventional steam

distillation technique would inevitably inflict thermal degradation to the natural

fragrance. In this experimental work, solvent extraction method using ethanol as solvent

was employed due to its mild extracting condition and lower operating cost. Three

different petal condition were used, which is dry petal,wet petal, and normal petal

respectively. The extract compositions were compared using gas chromatography

analysis. Preliminary results showed that volatile oil compounds were successfully

isolated from Jasmine flowers using these conditions. It was found that the main

constituents of the essential oils were benzyl acetate and benzyldehyde. Further studies

also revealed that the composition and yield of essential oils was mainly influenced by

the different types of petal condition used. The most optimum concentration which is

Benzyl Benzoate Concentration 2.6370% and Benzaldehyde Concentration 1.0780%

was extracted using dry petal condition . Low yield of the jasmine essential oils can be

improved in future study by carrying out the research in larger scale.

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ABSTRAK

Pati pengekstrakan minyak bunga melur terutamanya digunakan dalam

pembuatan minyak wangi dan mempunyai nilai komersil yang tinggi disebabkan oleh

ciri-ciri terapinya. Minyak ini adalah terdiri daripada komponen yang sensitif pada haba,

oleh itu penggunaan pengekstrakan wap air sebagai salah satu cara untuk

mengekstrakkan minyak ini secara tidak langsung membawa kepada kesan degradasi

haba terhadap bau semulajadi minyak bunga melur. Di dalam kajian ini, pengekstrakan

minyak ini dilakukan menggunakan kaedah penggunaan pelarut dengan menggunankan

pelarut ethanol kerana ia didapati sesuai untuk tujuan pengekstrakan minyak ini dan kos

menggunakan cara ini lebih rendah. Tiga jenis keadaan bunga yang digunakan bunga

kering, bunga lembap dan bunga normal. Sampel minyak yang didapati daripada kajian

ini akan dibandingkan menggunakan analisis gas kromatografi. Keputusan kajian pada

peringkat permulaan menunjukan beberapa komponen di dalam minyak ini dapat

dikesan menggunakan pelarut-pelarut ini. Komponen utama di dalam minyak bunga

melur yang telah dikenalpasti ialah benzil asetat dan benzaldehid. Kajian berikutnya

membuktikan pengesanan komponen dan kuantiti minyak ini adalah dipengaruhi oleh

faktor utamanya iaitu penggunaan keadaan bunga yang berlainan. Hasil minyak bunga

melur yang paling optimum iaitu peratusan kepekatan Benzyl Benzoate sebanyak

2.6370% dan Benzaldehyde sebanyak 1.0780% diekstrak menggunakan bunge melur

dalam keadaan kering . Hasil minyak bunga melur yang rendah ini dapat dipertingkatkan

pada kajian akan datang menggunakan skala yang lebih besar.

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TABLE OF CONTENTS

CHAPTER TITLE PAGE

ACKNOWLEDGEMENT iv ABSTRACT v ABSTRAK vi LIST OF TABLES x LIST OF FIGURES xi LIST OF ABBREVIATIONS xii LIST OF APPENDICES xiii

1 INTRODUCTION 1.1 Introduction 1 1.2 Problem Statement 3 1.3 Objective 4 1.4 Scope 4 2 LITERATURE REVIEW 2.1 Essential Oils Background 5 2.1.1 Properties and Uses of Essential Oils 8 2.1.2 Hazardous Essential Oils 10 2.1.2.1 Toxicity 10 2.1.2.2 Photo Toxicity 10 2.1.2.3 Pregnancy 11 2.1.2.4 High Blood Pressure 12 2.1.2.5 Dermal / Skin Irritation 12 2.1.3 Safety Information of Essential Oils 11

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2.2 Extraction Of Essential Oils 12 2.2.1 Introduction 12 2.2.2 Availability of Extraction Method 12 2.2.2.1 Supercritical Fluid Extraction 12 2.2.2.2 Solvent Extraction 12 2.2.2.3 Steam Distillation 14 2.2.2.4 Enfleurage 14 2.3 Jasmine Flower 15 2.3.1 A Background of Jasmine Flower 2.3.2 Benefits of Jasmine Flower 15 2.4 Essential Oils Quality 15 2.4.1 Specific gravity 15 2.4.2 Optical Rotation 16 2.4.3 Refractive Index 16 2.4.4 Gas Chromatography 17

3 METHODOLOGY 19 3.1 Introduction 19 3.2 Overall Methodology 19 3.3 Extraction Experimental Work 20

3.3.1 Sample Preparation 20 3.3.2 Apparatus and Procedure 21 3.3.2.1 Rotary Evaporator 21 3.3.2.2 Experimental Work 22 3.3.3 Analysis 3.3.3.1 Gas Chromatography 24 3.3.3.2 Identification of Essential Oils Constituents 24 3.3.3.3 Gas Chromatography-mass spectrometer 25 3.3.3.4 Calculation of yield of the essential oils. 26

4 RESULT AND DISCUSSION 4.1 Qualitative Analysis 27 4.1.1 GC Analysis Of Standard Benzyl Benzoate 27 4.1.2 GC Analysis of Standard Benzaldehyde 30 4.1.3 GC Analysis using Dry Petal Condition 33 4.1.4 GC Analysis using Normal Petal Condition 34 4.1.5 GC Analysis using Wet Petal Condition 35

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4.1.6 Concentrations of Benzaldehyde and Benzyl Benzoate in Jasmine Essential Oil Extract using different types of petal Condition 36

4.2 Quantitative Analysis 38 4.2.1 Efficiency of Extraction Process 38 4.2.2 Yield of Jasmine Essential Oil 38

5 CONCLUSION 5.1 Conclusion 40 5.2 Recommendation 41 REFERENCES 42 APPENDICES A 45

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LIST OF TABLES

TABLE NO TITLE PAGE

2.1 Essential Oils from Some Natural Plants. 7

2.2 Properties and Uses of the Top Essential Oils. 8

2.3 Brief Description of Jasmine Flower 13

3.1 Experimental Condition 22

4.1 Data concentration of two component in Jasmine Oil 36

4.2 Petal Conditions,Oil Dissolved In Solvent, Oil Recovery,

Efficiency 40

4.3 Petal Conditions , Amount of Flower Used, Oil recovery,

Yield 41

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LIST OF FIGURES

FIGURE TITLE PAGE

2.1 Jasmine Flower 16

3.1 Outline of the overall methodology 20

3.2 Rotary Evaporator 21

3.3 Overall Methodology of Solvent Extraction 23

3.4 Computerized GC System 24

3.5 Computerized GC-MS System 25

4.1 GC Analysis of Standard Benzyl Benzoate (1%) 28





4.6 GC Analysis of Standard Benzaldehyde (1%) 31





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4.11 GC Analysis of Sample Dry Petal Condition 34

4.12 GC Analysis of Sample Normal Petal Condition 35

4.13 GC Analysis of Sample Wet Petal Condition 36

4.14 Area versus Percent Concentration for Benzaldehyde 37

4.15 Area versus Percent Concentration for Benzyl Benzoate 37

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LIST OF ABBREVIATIONS

CO2 = Carbon dioxide

FID = Flame Ionization Detector

GC = Gas Chromatography

GC-MS = Gas Chromatography - Mass Spectrometer

RI = Refrective Index

SFE = Supercritical Fluids Extraction

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LIST OF APPENDICES

APPENDIX TITLE PAGE

A GC Analysis Result and component of Jasmine Essential Oils 45

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CHAPTER 1

INTRODUCTION 1.1 Introduction

Essential oils (EOs) are highly concentrated essences of aromatic plant.

Technically, it cannot be classified as perfumes or fragrance oils. It can be extracted

using a variety of methods such as steam distillation and solvent extraction. It is

widely used in perfumery, aromatherapy, cosmetics, incense, medicine, household

cleaning product as well as flavoring food and drink industries. EOs is also known as

volatile oils and ethereal oils. Sometime it may also be referred to as oil of the raw

plant materials from which it was extracted, for example oils of clave.

EOs can contain hundreds of organic constituents including hormones,

vitamin and other natural elements. Therefore, it is important to understand the effect

that the oils have and the way it works before using the EOs as part of an

aromatherapy treatment.

The name of the oil is the same as the name of the plant from which it is

derived. The function of the essential oil in the plant is not thoroughly understood. It

is probable that the odors of the flowers act as attractants (or repellents) for certain

insects, aiding in natural selection. Root oils, wood oils and leaf oils may act as a

protection against plant parasites and against depredations of animals. From the vast

number of species of plant that are known, about 3000 essential oils have been well

identified, though only some 150 have been exploited for commercial production

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A plant produces its essential oil in the protoplasm of its cells. The oil is an

excretion, which does not participate in the metabolism of the plant. The oils are rich

in energy and chemically very active; therefore, it is somewhat surprising for the

plant to expel such an amount of energy without making use of it. The oils are stored

in the form of micro droplets in the glands of the plants. After diffusing slowly

through the wall of the gland, these droplets spread out on the surface of the plant

before evaporating and filling the air with perfume.

There are many types of common essential oils; Rose, Bergamot, Lavender,

Jasmine and etc. Each of these raw materials requires different methods of

extraction. Plants like Rose and Jasmine which contains very little volatile oils needs

solvent-extracted since it is too delicate to be distilled. Hence chemical solvents such

as hexane and supercritical CO2 are employed to extract the important aromatic

ingredients.

Since the EOs is very sensitive to temperature and highly volatile, it requires

a high degree of expertise to extract the oils from the raw material because the

method used are time consuming and an expensive process.

Jasmine EOs has widespread applications. It can be used as antidepressant,

antiseptic, antispasmodic, and expectorant for dry skin, labor pains, cough, headache,

depression, exhaustion and sensitive skin. On top of that the aroma can be described

as warm, floral and exotic.

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1.2 Problem Statement

Jasmine flower contains very little volatile oil, and it needs to be solvent

extracted since it is too delicate to be distilled. Conventionally, chemical solvents are

employed to extract the important aromatic ingredients. In this study, supercritical

CO2 are used as solvent in supercritical extraction.

There are many other factors to be taken into consideration when producing a

good quality essential oil, which is important for its full benefit. Soil quality, climatic

and geographic conditions all contribute to the overall quality of the essential oil.

In some cases the length of cultivation is most important. Jasmine flowers

must be picked by hand at dawn on the very first day they open. In this project, the

Jasmine flower is being used as the substrate. Jasminum officinalis, or also known as

Melur in Malay Language, is commonly extracted for its essential oils using

methanol and ethanol as solvent. Conventional steam distillation method is not

suitable to process such material since it induces thermal degradation of many

compounds contained in the flower. The constituents of the Jasmine solvent-

extracted oils contain all the fragrance compounds (among others include benzyl

acetate, benzyl benzoate, linalool, phytol, fatty acid methyl ester and paraffins). The

latter compounds do not contribute to the scent of jasmine flowers. This extraction

product undergoes further processing to separate fragrance compounds from these

undesired co-extractives.

Solvent extraction uses very little heat so it is able to produce essential oils

from whose fragrance would otherwise be destroyed or altered during steam

distillation. Solvent extraction is used on delicate plants to produce higher amounts

of essential oils at lower cost. Other than the study on this method it is important to

improve the existing products of fragrance and also try to encourage the development

of local technologies to take advantage of market opportunities.

http://www.essential-oil-recipes.com/jasmine.html

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Each method of extraction actually has it own advantages and disadvantages.

This study is important in discovering solvent extraction method as the most optimal

methods for capturing the total spectrum of volatile constituent in this jasmine plant.

All in all, the study on this research is important in order to improve the effective

extraction based on flower petals’ conditions that affects production amount of

jasmine essential oil.

1.3 Objective

Due to the promising commercialization potential shown by Jasmine essential

oil, the main objective of this work is to carry out preliminary study on essential oils

and promote the best condition of flower for producing highest quantity of essential

oils.

1.4 Scope To achieve the above objectives, the following research scopes had been identified: i. Determination of the optimum conditions (petal condition) in extraction of

essential oils using solvent extraction

ii. Evaluation of the quality and yield of the jasmine extracted.

iii. Analysis of the product compositions obtained through this extraction process.

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CHAPTER 2

LITERATURE REVIEW 2.1 Essential Oils Background

Essential oils are liquid that is generally distilled from various parts of plant

that have strong aromatic components. These aromatic substances are made up of

different chemical compounds that can be found naturally in the plant, for instance,

alcohol, hydrocarbons, phenol, aldehydes, esters and ketones. Besides that, it may

also contain hundreds of organic constituents, including hormones, vitamins and

other natural elements. Essential oils 75 to 100 times more concentrated than the oils

in dried herbs.

For the plant, essential oils act as agent to attract or repel insects (odors of the

flowers); Leaf oils, wood oils, and root oils may serve to protect against plant

parasites or depredations by animals as well as anti-bacterial agent which is utilizing

the hormone in the oil. All in all there are only about 700 aromatic plants aromatic

among all types of plants in the world. Thus they are all important for the production

of essential oils.

Unlike fragrance oils or perfume, essential oils are derived from the true

plants. Perfume oils are unnaturally created fragrances since it contains artificial

substances. As such, it does not offer the therapeutic benefit that essential oils do.

Consequently pure essential oils are very expensive. Fortunately, they are also highly

effective because a few drops at a time are sufficient to achieve the desired effects.

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These oils could promote healing of the body and the mind. Typically, these essential

oils are used in three primary ways:

i. As odorants in cosmetics, perfumes, detergents, soap and etc

ii. As flavors in bakery goods, candies, meat, soft drinks, and also as food

additives.

iii. As pharmaceuticals in dental products and group of medicines.

Today, we could also easily find synthetic essential oils in the market where

the price would be cheaper than the pure ones. There are a few differences between

synthetic essential oils and pure essential oils. Synthetic essential oils are produced

by blending aromatic chemicals mostly derived from coal tar.

These oils may duplicate the smell of the pure essential oils, but the complex

chemical components of each essential oil created in nature determine its true

aromatic benefits. While synthetic essential oils are not suitable for aromatherapy,

they add an approximation of the natural scent to crafts, potpourri, soap and perfume

at a fraction of the cost. The reason of these synthetic products is mainly to reduce

the cost of production.

The oil of the essential oils bears the name of the plant from which it was

derived, for example Rose oil, and Bergamot oil. Such oils were called essential oils

because they were thought to represent the very essence of odors and flavors.

Essential oils can be divided into two broad categories:

I. Large volume oils which are usually distilled from leafy material, (e.g. lemon

grass, citronella and cinnamon leaves).

II. Small volume oils which are usually distilled from fruits, seed, buds and, to a

lesser extent, flowers, (e.g. cloves, nutmeg and coriander).

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Essential oils are the volatile oils distilled from aromatic plant materials. The

odor and flavor of the oils is usually dependent upon these oxygenated compounds.

Many oils are terpenoids; fews are benzene derivatives. Table 2.1 shows the

important constituents of the more common essential oils (Naik S.N., Lentz.H.,

1989).

Table 2.1: Essential Oils from Some Natural Plants.

Name Part of the

plant used Botanical name Important

constituents Uses

Lemongrass and citronella

Leaf Cymboposon spp Citral Citronella Terpenes

Perfumery Disinfectant

Eucalyptus Leaf Eucalyptus globules Eucalyptus citriodora Eucalyptus dives

Cineale Citronella Terpenes

Not mention

Cinnamon leaf

Leaf Cinnamon zeylanicum

Eugenol Used to make artificial vanilla

Clove Bud Eugenia caryophyllus

Eugenol Dentistry flavouring

Turpentine Not mention

Pinus spp Terpenes Paints

Lavender Flower Lavendula intermedia

Linalool Perfumery

Sandalwood Wood Santaium album

Sanatols Perfumery

Nutmeg Nut Myristica fragrans

Myristicin Not mention

Almond Nut Prunis communis

Benzaldehyde Not mention

Corainder Seed Coriandrum sativum

Linalool Terpenes

Not mention

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2.1.1 Properties and uses of the essential oils

Each essential oil has it own properties and uses which can be classified and

identified accordingly to the type of plant it was derived. Table 2.2 shows the

properties and uses of the top essential oil . From Table 2.2, it can be concluded that

the significant use of the essential oil is mainly contribute to pharmaceuticals

industry where most of it have the anti-depressant properties.

Table 2.2: Properties and Uses of the Top Essential Oils.

Essential

oil Biological

Name Properties Uses

Clory Sage Salvia Sclarea Warming, soothing, antiseptic, anticonvulsive, astringent, antiphlogistic, digestive, deodorant, tonic, uterine, bactericidal, antidepressant.

Menstrual problems, anxiety, depression, high blood pressure, acne boils, oily skin and hair, cramp, migraine, the genitor-urinary system disorders such as amenorrhoea, wrinkles, ulcers.

Eucalyptus Eucalyptus Globulus

Antiseptic, analgesic, antineuralgic, antirheumatic, antispasmodic, diuretic, expectorant, antiviral, hypoglycaemic, febrifuge, vulnerary, depurative, stimulant.

Muscular aches and pains, poor circulation, rheumatoid arthritis, asthma, bronchitis, flu, cold, epidermics, chicken pox, headaches, neuralgia, throat infections, skin disorders such as burns, cuts, herpes, wounds, insect bites.

Geranium Pelargonium Graveolens

Soothing, refreshing, relaxing, antidepressant, astringent, antiseptic, antihaemarrhagic, deodorant, diuretic, fungicidal, anti-inflammatory

Anxiety, adrenocortical glands and menopausal problems, sore throat, tonsillitis, cellulites, engorgement of breast, broken capillaries, eczema, hemorrhoids, oily complexion, mature skin, ulcers, wounds.

Jasmine Jasminum Officinale

Analgesic (mild), antidepressant, anti-inflammatory, antiseptic, antispasmodic, aphrodisiac, carminative, cicatrisant, expectorant, galactagogue, sedative, tonic (uterine)

Depression, nervous exhaustion and stress related conditions, jasmine is said to produce the feeling of optimism, confidence, euphoria, and it is especially good in cases of apathy, indifference, or listlessness.

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Jasmine is also used for catarrh, coughs, laryngitis, dysmenorrhoea, labor pains, uterine disorders, skin problem such as dry, greasy, irritated, sensitive skin, and for muscular spasms and sprains.

Lavender Lavendula Vera Officinalis

Analgesic, anticonclusive, antidepressant, antimicrobial, antirheumatic, antiseptic, antispasmodic, antitoxic, deodorant, sedative, diuretic, choleretic, hypotensive, stimulant, tonic, vulnery, cytophylatic, insecticide

Excellent first aid oil. It soothes cuts, bruises and insect bites. One of the most versatile therapeutic essences. For nervous system disorders such as depression, headache, hypertension, insomnia, migraine, sciatica, shock. Useful in treating skin conditions such as acne, allergies, athlete’s foot, boils, dandruff, dermatitis, sunburn, eczema. Treatment of disorders such as rheumatism, throat infections, flu, bronchitis, and asthma.

Lemon Citrus Limonum

Refreshing, antiseptic, stimulating, anti-anaemic, antirheumatic, antisclerotic, antitoxic, hypertensive, antiscorbutic, bactericidal, insecticidal, astringent, tonic,

Warts, depression, acne and indigestion, arthritis, cellulites, high blood pressure, nosebleeds, obesity, poor circulation, rheumatism, asthma, throat infections, bronchitis, cold, fever, flu. Treatment of anemia, brittle nails, corns, mouth ulcers, greasy skin, cuts, spots, and varicose veins.

Peppermint Menthe Piperita

Digestive, cooling, refreshing, mentally stimulating, analgesic, anti-inflammatory, antimicrobial, antiseptic, antiviral, astringent, expectorant, stomachic, hepatic, cordial, antispasmodic.

Muscle fatigue, bad breath, toothache, bronchitis, indigestion, and travel sickness, neuralgia, muscular pains, asthma, sinusitis, spasmodic cough, cramp, dyspepsia, skin problem such as acne, dermatitis, ringworm, scabies, and nausea.

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Ylang Ylang

Cananga Odorata ver genuina

Antidepressant, anti-infections, euphoric, relaxant, antiseptic, hypotensive, aphrodisiac, nervine, regulator, sedative (nervous), stimulant (circulatory), tonic

Depression, nervous tension, high blood pressure, hyperpnoea, (abnormally fast breathing), tachycardia, digestive upsets. For skin care such as hair growth, acne, hair rinse, oily skin, irritated and insect bites. For nervous system disorders such as frigidity, impotence, insomnia.

2.1.2 Hazardous essential oils Not all essential oil are safe to use in aromatherapy. This is due to the high

toxicity levels that the essential oils might have. Some of the oil can be hazardous as

they can cause severe dermal irritation and even damage the mucous membranes and

delicate stomach lining in undiluted form. Hence dermal application should be

avoided as a general practice; it is advisable to use essential oils only for external

remedies. Oils that fall under this category are bitter almond, calamus, camphor

(brown & yellow), cassia, cinnamon (bark), fennel (bitter), pine (dwarf), rue, sage

(common), thyme (red), wintergreen, garlic, onion, mustard and wormwood.

(Guidelines for Essential oils use 2003).

2.1.2.1 Toxicity

Essential oil such as Ajowan, Basil (exotic), Camphor (white), Cassia,

Cedarwood (Virginian), Cinnamon (leaf), clove (bud), coriander, Eucalyptus, fennel

(sweet), hyssop, juniper, nutmeg, pepper (black), sage (Spanish), tagetes, thyme

(white), turmeric, should be used only on dilution (at least 1:3) and for a maximum

of two weeks due to toxicity levels.

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i EXTRACTION OF ESSENTIAL OILS FROM JASMINE FLOWER US …